Condensed-cyclic compound and organic light-emitting diode including the same

ABSTRACT

A condensed-cyclic compound represented by Formula 1 below, and an organic light-emitting diode including the condensed-cyclic compound. 
     
       
         
         
             
             
         
       
     
     wherein R 1  through R 6 , Ar 5  and Ar 6 , and X 1  through X 10  are defined as in the specification.

CLAIM OF PRIORITY

This application is a continuation in part under 35 U.S.C. §120 of U.S.application Ser. No. 13/352,150, filed on Jan. 17, 2012 which is hereinincorporated by reference. This application also makes reference to,incorporates the same herein, and claims all benefits accruing under 35U.S.C. §119 from applications for CONDENSED-CYCLIC COMPOUND AND ORGANICLIGHT-EMITTING DIODE INCLUDING THE SAME earlier filed in the KoreanIntellectual Property Office on 17 Jan. 2011 and 13 Oct. 2011 and thereduly assigned Serial Nos. 10-2011-0004523 and 10-2011-0104825,respectively.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a condensed-cyclic compound representedby Formula 1 and an organic light-emitting diode including the same.

2. Description of the Related Art

Organic light-emitting diodes (OLEDs), which are self-emitting devices,have advantages such as a wide viewing angle, excellent contrast, quickresponse, high brightness, and excellent driving voltage. The OLEDs canprovide multicolored images.

A general OLED has a structure including a substrate, an anode, a holetransport layer (HTL), an emission layer (EML), an electron transportlayer (ETL), and a cathode which are sequentially stacked on thesubstrate. In this regard, the HTL, the EML, and the ETL are organiclayers formed of organic compounds.

An operating principle of an OLED having the above-described structureis as follows.

When a voltage is applied between the anode and the cathode, holesinjected from the anode move to the EML via the HTL, and electronsinjected from the cathode move to the EML via the ETL. The holes andelectrons recombine in the EML to generate excitons. When the excitonsdrop from an excited state to a ground state, light is emitted.

SUMMARY OF THE INVENTION

The present invention provides a condensed-cyclic compound having anovel structure.

The present invention also provides an organic light-emitting diodeincluding the above condensed-cyclic compound.

According to an aspect of the present invention, there is provided acondensed-cyclic compound represented by Formula 1 below:

wherein R₁ may be represented by —(Ar₁)_(a1)—(R₁₁)_(b1), R₂ may berepresented by —(Ar₂)_(a2)—(R₁₂)_(b2), R₃ may be represented by—(Ar₃)_(a3)—(R₁₃)_(b3), and R₄ may be represented by—(Ar₄)_(a4)—(R₁₄)_(b4); Ar₁ through Ar₄ may be each independently asubstituted or unsubstituted C₆-C₆₀ aromatic linking group or asubstituted or unsubstituted C₂-C₆₀ heteroaromatic linking group; Ar_(y)and Ar₆ may be each independently a substituted or unsubstituted C₆-C₆₀arylene group or a substituted or unsubstituted C₂-C₆₀ heteroarylenegroup; R₅, R₆, and R₁₁ through R₁₄ may be each independentlynon-covalent electron pairs, hydrogen, deuterium, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group,a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, or a substituted or unsubstitutedC₂-C₆₀ condensed-cyclic group; a₁ through a₄ may be each independentlyan integer of 0 to 3; b₁ through b₄ may be each independently an integerof 1 to 5; c and d may be each independently an integer of 0 to 3; X₁through X₁₀ may be each independently hydrogen, deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, —Si(R₂₁)(R₂₂)(R₂₃), or —N(R₂₄)(R₂₅); and R₂₁ through R₂₅ may beeach independently hydrogen, deuterium, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, or a substituted or unsubstitutedC₂-C₆₀ heteroaryl group.

In some embodiments of the present invention, R₁₁ through R₁₄ in Formula1 may be each independently hydrogen, deuterium, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted phenylgroup, a substituted or unsubstituted pentalenyl group, a substituted orunsubstituted indenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted azulenyl group, a substituted orunsubstituted heptalenyl group, a substituted or unsubstituted indacenylgroup, a substituted or unsubstituted acenaphthyl group, a substitutedor unsubstituted fluorenyl group, a substituted or unsubstitutedphenalenyl group, a substituted or unsubstituted phenanthrenyl group, asubstituted or unsubstituted anthryl group, a substituted orunsubstituted fluoranthenyl group, a substituted or unsubstitutedtriphenylenyl group, a substituted or unsubstituted pyrenyl group, asubstituted or unsubstituted chrysenyl group, a substituted orunsubstituted naphthacenyl group, a substituted or unsubstituted picenylgroup, a substituted or unsubstituted perylenyl group, a substituted orunsubstituted pentaphenyl group, a substituted or unsubstitutedhexacenyl group, a substituted or unsubstituted cyclopentyl group, asubstituted or unsubstituted cyclohexyl group, a substituted orunsubstituted cycloheptyl group, a substituted or unsubstituteddihydronaphthyl group, a substituted or unsubstituted tetrahydronaphthylgroup, or a substituted or unsubstituted dihydro-indenyl group.

In some embodiments of the present invention, Ar₁ through Ar₄ in Formula1 may be each independently a substituted or unsubstituted benzenelinking group, a substituted or unsubstituted pentalene linking group, asubstituted or unsubstituted indene linking group, a substituted orunsubstituted naphthalene linking group, a substituted or unsubstitutedazulene linking group, a substituted or unsubstituted heptalene linkinggroup, a substituted or unsubstituted indacene linking group, asubstituted or unsubstituted acenaphthylene linking group, a substitutedor unsubstituted fluorene linking group, a substituted or unsubstitutedphenalene linking group, a substituted or unsubstituted phenanthrenelinking group, a substituted or unsubstituted anthracene linking group,a substituted or unsubstituted_fluoranthene linking group, a substitutedor unsubstituted triphenylene linking group, a substituted orunsubstituted pyrene linking group, a substituted or unsubstitutedcrycene linking group, a substituted or unsubstituted naphthacenelinking group, a substituted or unsubstituted pycene linking group, asubstituted or unsubstituted perylene linking group, a substituted orunsubstituted pentacene linking group, or a substituted or unsubstitutedhexacene linking group.

In some embodiments of the present invention, a₁ through a₄ in Formula 1may be each independently 0, 1, or 2, and b₁ through b₄ may be eachindependently 1 or 2.

In some embodiments of the present invention, R₁₁ through R₁₄ in Formula1 may be each independently one of hydrogen; deuterium; a C₁-C₁₀ alkylgroup; a phenyl group; a naphthyl group; a phenanthrenyl group; afluorenyl group; a pyrenyl group; a cyclopentyl group; a cyclohexylgroup; a tetrahydronaphthyl group; a dihydro-indenyl group; and a phenylgroup, a naphthyl group, a phenanthrenyl group, a fluorenyl group, apyrenyl group, a cyclopentyl group, a cyclohexyl group, atetrahydronaphthyl group, and a dihydro-indenyl group that aresubstituted with at least one of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, and —Si(Q₁)(Q₂)(Q₃); Q₁ through Q₃ may be eachindependently a C₁-C₁₀ alkyl group or a C₆-C₁₄ aryl group; Ar₁ throughAr₄ may be each independently represented by one of Formulae 3A through3G below.

Wherein Z₁₁ through Z₁₄ may be each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group; s may be an integer of 1to 6; and t may be an integer of 1 to 3.

In some embodiments of the present invention, R₅ and R₆ in Formula 1 maybe each independently hydrogen, deuterium, a substituted orunsubstituted C₁-C₁₀ alkyl group, or a substituted or unsubstitutedC₆-C₂₀ aryl group.

In some embodiments of the present invention, R₅ and R₆ in Formula 1 maybe each independently one of hydrogen; deuterium; a C₁-C₁₀ alkyl group;a phenyl group; a naphthyl group; and a phenyl group and a naphthylgroup that are substituted with at least one of deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino_group, anamidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, and a C₁-C₆₀ alkoxy group.

In some embodiments of the present invention, R₅ and R₆ in Formula 1 maybe linked to each other via a single bond, a linking group representedby Formula 4A below, or a linking group represented by Formula 4B below.

Wherein X₂₁ through X₂₃ may be each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₂-C₆₀heteroaryl group.

In some embodiments of the present invention, the condensed-cycliccompound of Formula 1 may include one of the compounds represented byFormulae 1A through 1D below:

wherein R₁ through R₄, Ar₅, Ar₆, c, d, X₁ through X₁₀, and X₂₁ throughX₂₃ are the same as defined above.

Z₂₁ and Z₂₂ may be each independently hydrogen, deuterium, a halogenatom, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof,a sulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, or a substituted or unsubstitutedC₁-C₆₀ alkoxy group; u may be an integer of 1 to 4; and v may be aninteger of 1 to 6.

In some embodiments of the present invention, at least one of acombination of R₁ and R₂ and a combination of R₃ and R₄ in Formula 1 maybe linked to each other.

In some embodiments of the present invention, at least one of —N(R₁)(R₂)and —N(R₃)(R₄) in Formula 1 may be represented by one of Formulae 5Athrough 5F below.

Wherein Z₃₁ through Z₄₂ may be each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, or a substituted or unsubstitutedC₁-C₆₀ alkoxy group, or a substituted or unsubstituted C₆-C₆₀ arylgroup; and w and x may be each independently an integer of 1 to 8.

In some embodiments of the present invention, the condensed-cycliccompound may be one of Compounds 1, 3, 9, 10, 11, 12, 14, 17, 22, 26,28, 29, 54, 64, and 68:

According to another aspect of the present invention, there is providedan organic light-emitting diode including a first electrode; a secondelectrode facing the first electrode; and an organic layer interposedbetween the first electrode and the second electrode, wherein theorganic layer includes at least one of the condensed-cyclic compounds ofFormula 1.

In some embodiments of the present invention, the organic layer mayinclude at least one of a hole injection layer, a hole transport layer,a functional layer having hole injection and hole transport abilities,an emission layer, an electron transport layer, and an electroninjection layer

In some embodiments of the present invention, the emission layer mayinclude the condensed-cyclic compound.

In some embodiments of the present invention, the emission layer mayinclude a host and the condensed-cyclic compound in the emission layeracts as a dopant.

In some embodiments of the present invention, the host may include ananthracene-based compound represented by Formula 60 below.

Wherein Ar₁₁ and Ar₁₂ may be each independently a substituted orunsubstituted C₆-C₆₀ arylene group; Ar₁₃ and Ar₁₄ may be eachindependently a substituted or unsubstituted C₁-C₁₀ alkyl group or asubstituted or unsubstituted C₆-C₆₀ aryl group; and e and f may be eachindependently an integer of 0 to 5.

In some embodiments of the present invention, the electron transportlayer may include an electron transport organic compound and ametal-containing material.

In some embodiments of the present invention, the metal-containingmaterial may be a lithium complex.

In some embodiments of the present invention, the organic layer mayinclude at least one of a hole injection layer, a hole transport layer,and a functional layer having hole injection and hole transportabilities, and at least one of the hole injection layer, the holetransport layer, and the functional layer having hole injection and holetransport abilities comprises a charge-generating material.

BRIEF DESCRIPTION OF THE DRAWINGS

A more complete appreciation of the present invention, and many of theattendant advantages thereof, will be readily apparent as the presentinvention becomes better understood by reference to the followingdetailed description when considered in conjunction with theaccompanying drawings in which like reference symbols indicate the sameor similar components, wherein:

FIG. 1 is a schematic structure of an organic light-emitting diode(OLED) according to an embodiment of the present invention;

FIG. 2 is a graph showing lifetime characteristics of OLEDs manufacturedaccording to Examples 1 through 4 and Comparative Example 1 according toan embodiment of the present invention;

FIG. 3 is a graph showing lifetime characteristics of OLEDs manufacturedaccording to Examples 5 through 8 and Comparative Example 2 according toan embodiment of the present invention;

FIG. 4 is a graph showing changes in current density versus voltagecharacteristics of OLEDs of Examples 5 through 8 and Comparative Example2 according to an embodiment of the present invention; and

FIG. 5 is a graph showing changes in current density versus voltagecharacteristics of OLEDs of Examples 1 through 4 and Comparative Example1 according to an embodiment of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present invention will be described more fully withreference to the accompanying drawings, in which exemplary embodimentsof the present invention are shown.

As used herein, the term “and/or” includes any and all combinations ofone or more of the associated listed items. Expressions such as “atleast one of” when preceding a list of elements, modify the entire listof elements and do not modify the individual elements of the list.

According to an embodiment of the present invention, there is provided acondensed-cyclic compound represented by Formula 1 below:

Wherein R₁ may be represented by —(Ar₁)_(a1)—(R₁₁)_(b1), R₂ may berepresented by —(Ar₂)_(a2)—(R₁₂)_(b2), R₃ may be represented by—(Ar₃)_(a3)—(R₁₃)_(b3), and R₄ may be represented by—(Ar₄)_(a4)—(R₁₄)_(b4); R₅ and R₆ may be each independently non-covalentelectron pairs, hydrogen, deuterium, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstitutedC₂-C₆₀ heteroaryl group, or a substituted or unsubstituted C₂-C₆₀condensed-cyclic group.

In Formula 1, R₁₁ through R₁₄ may be each independently non-covalentelectron pairs, hydrogen, deuterium, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstitutedC₂-C₆₀ heteroaryl group, or a substituted or unsubstituted C₂-C₆₀condensed-cyclic group.

For example, R₁₁ through R₁₄ may be each independently hydrogen,deuterium, a substituted or unsubstituted C₁-C₁₀ alkyl group, asubstituted or unsubstituted phenyl group, a substituted orunsubstituted pentalenyl group, a substituted or unsubstituted indenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted azulenyl group, a substituted or unsubstituted heptalenylgroup, a substituted or unsubstituted indacenyl group, a substituted orunsubstituted acenaphthyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted phenalenyl group, asubstituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthryl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenylenyl group,a substituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstitutednaphthacenyl group, a substituted or unsubstituted picenyl group, asubstituted or unsubstituted perylenyl group, a substituted orunsubstituted pentaphenyl group, a substituted or unsubstitutedhexacenyl group, a substituted or unsubstituted cyclopentyl group, asubstituted or unsubstituted cyclohexyl group, a substituted orunsubstituted cycloheptyl group, a substituted or unsubstituteddihydronaphthyl group, a substituted or unsubstituted tetrahydronaphthylgroup, or a substituted or unsubstituted dihydro-indenyl group, but arenot limited thereto.

R₁₁ through R₁₄ may be each independently one of hydrogen; deuterium; aC₁-C₁₀ alkyl group; a phenyl group; a naphthyl group; a phenanthrenylgroup; a fluorenyl group; a pyrenyl group; a cyclopentyl group; acyclohexyl group; a tetrahydronaphthyl group; a dihydro-indenyl group;and a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenylgroup, a pyrenyl group, a cyclopentyl group, a cyclohexyl group, atetrahydronaphthyl group, and a dihydro-indenyl group that aresubstituted with at least one of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, and —Si(Q₁)(Q₂)(Q₃); Q₁ through Q₃ are eachindependently a C₁-C₁₀ alkyl group or a C₆-C₁₄ aryl group.

For example, R₁₁ through R₁₄ may be each independently hydrogen,deuterium, or a group represented by one of Formulae 2A through 2Kbelow, but are not limited thereto:

In Formulae 2A through 2K, Z₁ through Z₄ may be each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group(e.g., a C₁-C₁₀ alkyl group), a C₂-C₆₀ alkenyl group (e.g., C₂-C₁₀alkenyl group), a C₂-C₆₀ alkynyl group (e.g., a C₂-C₁₀ alkynyl group), aC₁-C₆₀ alkoxy group (e.g., a C₁-C₁₀ alkoxy group), or —Si(Q₁)(Q₂)(Q₃); pis an integer of 1 to 11; and q is an integer of 1 to 4. In this regard,Q₁ through Q₃ may be each independently a C₁-C₁₀ alkyl group or a C₆-C₁₄aryl group.

For example, in Formulae 2A through 2K, Z₁ through Z₄ may be eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid or a salt thereof, a methyl group, anethyl group, a propyl group, a butyl group, a pentyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pentoxygroup, or —Si(Q₁)(Q₂)(Q₃) where Q₁ through Q₃ may be each independentlya C₁-C₁₀ alkyl group (e.g., a methyl group, an ethyl group, a propylgroup, a butyl group, a pentyl group, and the like).

In Formulae 2A through 2K, * denotes a binding site with “N” of Formula1 when each of a1 through a4 is 0 and denotes a binding site with eachof Ar₁ through Ar₄ when each of a1 through a4 is not 0.

In Formula 1, Ar₁ through Ar₄ may be each independently a substituted orunsubstituted C₆-C₆₀ aromatic linking group or a substituted orunsubstituted C₂-C₆₀ heteroaromatic linking group. Ar₁ through Ar₄ maybe each independently a divalent linking group (refer to Formula 3Abelow), a trivalent linking group (refer to Formula 3C below), atetravalent linking group, or a pentavalent group according to thenumber of each of R₁₁ groups to R₁₄ groups that are respectively linkedto Ar₁ through Ar₄, and this may be easily understood with reference toCompounds 1 through 78 below, which are condensed-cyclic compounds.

In Formula 1, Ar₁ through Ar₄ may be each independently a substituted orunsubstituted benzene linking group, a substituted or unsubstitutedpentalene linking group, a substituted or unsubstituted indene linkinggroup, a substituted or unsubstituted naphthalene linking group, asubstituted or unsubstituted azulene linking group, a substituted orunsubstituted heptalene linking group, a substituted or unsubstitutedindacene linking group, a substituted or unsubstituted acenaphthylenelinking group, a substituted or unsubstituted fluorene linking group, asubstituted or unsubstituted phenalene linking group, a substituted orunsubstituted phenanthrene linking group, a substituted or unsubstitutedanthracene linking group, a substituted or unsubstituted fluoranthenelinking group, a substituted or unsubstituted triphenylene linkinggroup, a substituted or unsubstituted pyrene linking group, asubstituted or unsubstituted crycene linking group, a substituted orunsubstituted naphthacene linking group, a substituted or unsubstitutedpycene linking group, a substituted or unsubstituted perylene linkinggroup, a substituted or unsubstituted pentacene linking group, or asubstituted or unsubstituted hexacene linking group.

For example, Ar₁ through Ar₄ may be each independently represented byone of Formulae 3A through 3G below:

In Formulae 3A through 3G, Z₁₁ through Z₁₄ may be each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group(e.g., a C₁-C₁₀ alkyl group), a C₂-C₆₀ alkenyl group (e.g., C₂-C₁₀alkenyl group), a C₂-C₆₀ alkynyl group (e.g., a C₂-C₁₀ alkynyl group),or a C₁-C₆₀ alkoxy group (e.g., a C₁-C₁₀ alkoxy group); s is an integerof 1 to 6; and t is an integer of 1 to 3.

For example, in Formulae 3A through 3G, Z₁₁ through Z₁₄ may be eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid or a salt thereof, a methyl group, anethyl group, a propyl group, a butyl group, a pentyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, or a pentoxygroup, but are not limited thereto.

In Formulae 3A through 3G, * denotes a binding site with “N” of Formula1 and *′ denotes a binding site with each of R₁₁ through R₁₄.

In Formula 1, a₁ through a₄ may be each independently an integer of 0 to3 and b₁ through b₄ may be each independently an integer of 1 to 5. Forexample, a₁ through a₄ may be each independently an integer of 0, 1, or2 and b₁ through b₄ may be each independently an integer of 1 or 2, butthey are not limited thereto. If a₁ is 2 or more, two or more Ar₁ groupsmay be identical to or different from each other. If a₂ is 2 or more,two or more Ar₂ groups may be identical to or different from each other.If a₃ is 2 or more, two or more Ar₃ groups may be identical to ordifferent from each other. If a₄ is 2 or more, two or more Ar₄ groupsmay be identical to or different from each other. If b₁ is 2 or more,two or more R₁₁ groups may be identical to or different from each other.If b₂ is 2 or more, two or more R₁₂ groups may be identical to ordifferent from each other. If b₃ is 2 or more, two or more R₁₃ groupsmay be identical to or different from each other. If b₄ is 2 or more,two or more R₁₄ groups may be identical to or different from each other.

With reference to the description above, in Formula 1, R₁ through R₄ maybe selected. For example, R₁ through R₄ may be each independentlyselected such that R₁₁ through R₁₄ are each independently one selectedfrom hydrogen; deuterium; a C₁-C₁₀ alkyl group; a phenyl group; anaphthyl group; a phenanthrenyl group; a fluorenyl group; a pyrenylgroup; a cyclopentyl group; a cyclohexyl group; a tetrahydronaphthylgroup; a dihydro-indenyl group; and a phenyl group, a naphthyl group, aphenanthrenyl group, a fluorenyl group, a pyrenyl group, a cyclopentylgroup, a cyclohexyl group, a tetrahydronaphthyl group, and adihydro-indenyl group that are substituted with at least one ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, and—Si(Q₁)(Q₂)(Q₃) where Q₁ through Q₃ are each independently a C₁-C₁₀alkyl group or a C₆-C₁₄ aryl group; and Ar₁ through Ar₄ are eachindependently represented by one of Formulae 3A through 3G.

Alternatively, R₁ through R₄ may be each independently selected suchthat R₁₁ through R₁₄ are each independently hydrogen or deuterium, orrepresented by one of Formulae 2A through 2K, and Ar₁ through Ar₄ areeach independently represented by one of Formulae 3A through 3G, but arenot limited thereto.

In Formula 1, R₁ through R₄ may be identical to or different from eachother.

In Formula 1, Ar₅ and Ar₆ may be each independently a substituted orunsubstituted C₆-C₆₀ arylene group, or a substituted or unsubstitutedC₂-C₆₀ heteroarylene group.

For example, Ar₅ and Ar₆ may be each independently a substituted orunsubstituted phenylene group, a substituted or unsubstitutedpentalenylene group, a substituted or unsubstituted indenylene group, asubstituted or unsubstituted naphthylene group, a substituted orunsubstituted azulenylene group, a substituted or unsubstitutedheptalenylene group, a substituted or unsubstituted indacenylene group,a substituted or unsubstituted acenaphthylene group, a substituted orunsubstituted fluorenylene group, a substituted or unsubstitutedphenalenylene group, a substituted or unsubstituted phenanthrenylenegroup, a substituted or unsubstituted anthrylene group, a substituted orunsubstituted fluoranthenylene group, a substituted or unsubstitutedtriphenylenylene group, a substituted or unsubstituted pyrenylene group,a substituted or unsubstituted chrysenylene group, a substituted orunsubstituted naphthacenylene group, a substituted or unsubstitutedpycenylene group, a substituted or unsubstituted perylenylene group, asubstituted or unsubstituted pentacenylene group, or a substituted orunsubstituted hexacenylene group.

For example, R₅ and R₆ are each independently hydrogen, deuterium, asubstituted or unsubstituted C₁-C₁₀ alkyl group, or a substituted orunsubstituted C₆-C₂₀ aryl group.

For example, R₅ and R₆ may be each independently one of hydrogen;deuterium; a C₁-C₁₀ alkyl group; a phenyl group; a naphthyl group; and aphenyl group and a naphthyl group that are substituted with at least oneof deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group(e.g., methyl, ethyl, propyl, butyl, pentyl, and the like), a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group (e.g.,methoxy, ethoxy, propoxy, butoxy, pentoxy, and the like), but are notlimited thereto.

In Formula 1, c and d may be each independently an integer of 0 to 3.For example, c and d may be each independently an integer of 0 or 1, butare not limited thereto.

In Formula 1, R₅ and R₆ may be linked to each other via a single bond, alinking group represented by Formula 4A below, or a linking grouprepresented by Formula 4B below:

Wherein X₂₁ through X₂₃ may be each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₂-C₆₀heteroaryl group.

For example, in Formulae 4A and 4B, X₂₁ through X₂₃ may be eachindependently one of hydrogen; deuterium; a halogen atom; a hydroxylgroup; a cyano group; a nitro group; an amino group; an amidino group;hydrazine; hydrazone; a carboxyl group or a salt thereof; a sulfonicacid group or a salt thereof; a phosphoric acid or a salt thereof; aC₁-C₁₀ alkyl group; a phenyl group; a naphthyl group; and a phenyl groupand a naphthyl group that are substituted with at least one ofdeuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group(e.g., methyl, ethyl, propyl, butyl, pentyl, and the like), a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group (e.g.,methoxy, ethoxy, propoxy, butoxy, pentoxy, and the like), but are notlimited thereto.

When R₅ and R₆ of Formula 1 are linked to each other via a single bond,a linking group of Formula 4A, or a linking group of Formula 4B asdescribed above, the condensed-cyclic compound may be represented by oneof Formulae 1A through 1D (in Formula 1, each of R₅ and R₆ isindependently a substituted or unsubstituted phenyl group):

Wherein R₁ through R₄, Ar₅, Ar₆, c, d, X₁ through X₁₀, and X₂₁ throughX₂₃ are the same as defined above; Z₂₁ and Z₂₂ may be each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, or asubstituted or unsubstituted C₁-C₆₀ alkoxy group; u may be an integer of1 to 4; and v may be an integer of 1 to 6.

For example, in Formulae 1A through 1D, Z₂₁ and Z₂₂ may be eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid or a salt thereof, a methyl group, anethyl group, a propyl group, a butyl group, a pentyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, or a pentoxygroup, but are not limited thereto.

In Formula 1, at least one of a combination of R₁ and R₂ and acombination of R₃ and R₄ may be linked to each other. For example, inFormula 1, at least one of —N(R₁)(R₂) and —N(R₃)(R₄) may be representedby one of Formulae 5A through 5F below, but are not limited thereto:

Wherein Z₃₁ through Z₄₂ may be each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, or a substituted or unsubstitutedC₁-C₆₀ alkoxy group, or a substituted or unsubstituted C₆-C₆₀ arylgroup; and w and x may be each independently an integer of 1 to 8.

For example, in Formulae 5A through 5F, Z₃₁ through Z₄₂ may be eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group ora salt thereof, a phosphoric acid or a salt thereof, a methyl group, anethyl group, a propyl group, a butyl group, a pentyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pentoxygroup, a phenyl group, a naphthyl group, or an anthryl group, but arenot limited thereto.

For example, in Formula 1, at least one of —N(R₁)(R₂) and —N(R₃)(R₄) maybe represented by one of Formulae 6A through 6F below, but are notlimited thereto:

In Formulae 6A through 6F, a detailed description of Z₃₁, Z₃₂, Z₃₃, Z₃₄,Z₃₅, and Z₄₂ is already provided above. For example, Z₃₁, Z₃₂, Z₃₃, Z₃₄,and Z₃₅ may be each independently hydrogen or a substituted orunsubstituted C₁-C₁₀ alkyl group, and Z₄₂ may be a phenyl group, anaphthyl group, or an anthryl group.

In Formula 1, X₁ through X₁₀ may be each independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group,a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, —Si(R₂₁)(R₂₂)(R₂₃), or—N(R₂₄)(R₂₅); and where R₂₁ through R₂₅ may be each independentlyhydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀ alkyl group,a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₂-C₆₀heteroaryl group.

For example, in Formula 1, X₁ through X₁₀ may be each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted C₁-C₁₀alkoxy group, or a substituted or unsubstituted C₆-C₁₄ aryl group. Atleast two adjacent substituents of X₁ through X₁₀ may be linked to eachother to form a saturated or unsaturated ring.

The condensed-cyclic compound may be one of Compounds 1 through 78below, but is not limited thereto; wherein TMS is trimethyl silyl:

In some embodiments of the present invention, the condensed-cycliccompound may be one of Compounds 1A through 3A and 5A to 30A below, butis not limited thereto; wherein TMS is trimethyl silyl:

Examples of the unsubstituted C₁-C₆₀ alkyl group (or C₁-C₆₀ alkyl group)include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl,hexyl, and the like. The substituted C₁-C₆₀ alkyl group may be a groupin which at least one hydrogen of the unsubstituted C₁-C₆₀ alkyl groupis substituted with deuterium; a halogen atom; a hydroxyl group; a cyanogroup; a nitro group; an amino group; an amidino group; hydrazine;hydrazone; a carboxyl group or a salt thereof; a sulfonic acid group ora salt thereof; a phosphoric acid or a salt thereof; a C₁-C₆₀ alkylgroup; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxygroup; a C₃-C₆₀ cycloalkyl group; a C₆-C₆₀ aryl group; a C₆-C₆₀ aryloxygroup; a C₆-C₆₀ arylthio group; a C₂-C₆₀ heteroaryl group; a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀ cycloalkyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, or a C₂-C₆₀ heteroaryl groupthat is substituted with at least one of deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, and a C₁-C₆₀ alkoxy group; —N(Q₁)(Q₂); or —Si(Q₃)(Q₄)(Q₅) (Q₁through Q₅ maybe be each independently a C₃-C₆₀ cycloalkyl group; aC₆-C₆₀ aryl group; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ arylthio group; aC₂-C₆₀ heteroaryl group); and a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, a C₃-C₆₀cycloalkyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀arylthio group, or a C₂-C₆₀ heteroaryl group that is substituted with atleast one of deuterium, a halogen atom, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group.

The unsubstituted C₁-C₆₀ alkoxy group (or C₁-C₆₀ alkoxy group) has aformula of —OA (in this regard, A is the unsubstituted C₁-C₆₀ alkylgroup as described above) and examples thereof include methoxy, ethoxy,isopropyloxy, and the like. At least one hydrogen atom of theunsubstituted C₁-C₆₀ alkoxy group may be substituted with the samesubstituent as in the substituted C₁-C₆₀ alkyl group described above.

The unsubstituted C₂-C₆₀ alkenyl group (or C₂-C₆₀ alkenyl group) isinterpreted to contain at least one carbon-carbon double bond in thecenter or at a terminal of the unsubstituted C₂-C₆₀ alkyl group.Examples of the unsubstituted C₂-C₆₀ alkenyl group include ethenyl,propenyl, butenyl, and the like. At least one hydrogen atom of theunsubstituted C₂-C₆₀ alkenyl group may be substituted with thesubstituents described with reference to the substituted C₁-C₆₀ alkylgroup described above.

The unsubstituted C₂-C₆₀ alkynyl group (or C₂-C₆₀ alkynyl group) isinterpreted to contain at least one carbon-carbon triple bond in thecenter or at a terminal of the C₂-C₆₀ alkyl group defined above.Examples of the unsubstituted C₂-C₆₀ alkynyl group include ethynyl,propynyl, and the like. At least one hydrogen atom of the unsubstitutedC₂-C₆₀ alkynyl group may be substituted with the substituents describedwith reference to the substituted C₁-C₆₀ alkyl group described above.

The unsubstituted C₆-C₆₀ aryl group indicates a monovalent group havingan aromatic carbocyclic system that has 5 to 60 carbon atoms and atleast one aromatic ring and the unsubstituted C₆-C₆₀ arylene groupindicates a divalent group having an aromatic carbocyclic system thathas 5 to 60 carbon atoms and at least one aromatic ring. If the C₆-C₆₀aryl group and the C₆-C₆₀ arylene group each independently have two ormore aromatic rings, the rings may be fused with each other. At leastone hydrogen atom of each of the unsubstituted C₆-C₆₀ aryl group and theunsubstituted C₆-C₆₀ arylene group may be substituted with thesubstituents described with reference to the substituted C₁-C₆₀ alkylgroup described above.

Examples of the unsubstituted C₆-C₆₀ aryl group include, but are notlimited to, a phenyl group, a C₁-C₁₀ alkylphenyl group (e.g., anethylphenyl group), a C₁-C₁₀ alkylbiphenyl group (e.g., an ethylbiphenylgroup), a halophenyl group (e.g., an o-, m- and p-fluorophenyl group,and a dichlorophenyl group), a dicyanophenyl group, atrifluoromethoxyphenyl group, an o-, m-, and p-tolyl group, an o-, m-and p-cumenyl group, a mesityl group, a phenoxyphenyl group, an(α,α-dimethylbenzene)phenyl group, a (N,N′-dimethyl)aminophenyl group, a(N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group,a naphthyl group, a halonaphthyl group (e.g., a fluoronaphthyl group), aC₁-C₁₀ alkylnaphthyl group (e.g., a methylnaphthyl group), a C₁-C₁₀alkoxynaphthyl group (e.g., a methoxynaphthyl group), an anthracenylgroup, an azulenyl group, a heptalenyl group, an acenaphthylenyl group,a phenalenyl group, a fluorenyl group, an anthraquinolyl group, amethylanthryl group, a phenanthryl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenylgroup, a perylenyl group, a chloroperylenyl group, a pentaphenyl group,a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, ahexacenyl group, a rubicenyl group, a coroneryl group, a trinaphthylenylgroup, a heptaphenyl group, a heptacenyl, a pyranthrenyl group, and anovalenyl group.

Examples of the substituted C₆-C₆₀ aryl group may be easily understoodwith reference to the examples of the unsubstituted C₆-C₆₀ aryl groupdescribed above and the substituents of the substituted C₁-C₆₀ alkylgroup described above.

Examples of the substituted or unsubstituted C₆-C₆₀ arylene group may beeasily understood with reference to the substituted or unsubstitutedC₆-C₆₀ aryl group described above.

The unsubstituted C₂-C₆₀ heteroaryl group indicates a monovalent grouphaving at least one aromatic ring system including carbon rings and atleast one hetero atom selected from the group consisting of N, O, P, andS, and the unsubstituted C₂-C₆₀ heteroarylene group indicates a divalentgroup having at least one aromatic ring system including carbon ringsand at least one hetero atom selected from the group consisting of N, O,P, and S. In this regard, if the C₂-C₆₀ heteroaryl group and the C₂-C₆₀heteroarylene group each independently have two or more aromatic rings,the rings may be fused with each other. At least one hydrogen atom ofeach of the unsubstituted C₂-C₆₀ heteroaryl group and the unsubstitutedC₂-C₆₀ heteroarylene group may be substituted with the substituentsdescribed with reference to the substituted C₁-C₆₀ alkyl group describedabove.

Examples of the unsubstituted C₂-C₆₀ heteroaryl group include, but arenot limited to, a pyrazolyl group, an imidazolyl group, an oxazolylgroup, a thiazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinylgroup, a triazinyl group, a carbazolyl group, an indolyl group, aquinolinyl group, an isoquinolinyl group, a benzoimidazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group. Examples of thesubstituted or unsubstituted C₂-C₆₀ heteroarylene group may be easilyunderstood with reference to the examples of the substituted orunsubstituted C₂-C₆₀ heteroarylene group described above.

The substituted or unsubstituted C₆-C₆₀ aryloxy group has a formula of—OA₂ wherein A₂ is the substituted or unsubstituted C₆-C₆₀ aryl group asdescribed above, and the substituted or unsubstituted C₆-C₆₀ arylthiogroup has a formula of —SA₃ wherein A₃ is the substituted orunsubstituted C₆-C₆₀ aryl group described above.

The condensed-cyclic compound of Formula 1 may be synthesized using awell-known organic synthesis method. The synthesis method of thecondensed-cyclic compound of Formula 1 may be easily understood by oneof ordinary skill in the art with reference to Examples, which will bedescribed later.

The condensed-cyclic compound of Formula 1 may have excellent thermalresistance and luminous properties. In particular, A-site carbon andB-site carbon of Formula 1 are linked respectively to —N(R₁)(R₂) and—N(R₃)(R₄), optionally, via Ar₅ and Ar₆, respectively.

In general, when conjugation lengths of backbone in condensed ringsbecome longer, the band gap becomes smaller and thus the emissionwavelength moves to longer wavelengths. On the other hand, thecondensed-cyclic compound of Formula 1 has a structure in which theC-site carbon is broken conjugation of condensed rings between theA-site carbon and the B-site carbon as shown in Formula 1 below. Each ofthe C-site carbon, A-site carbon and B-site carbon is linked to an aminegroup and thus may form a wider band gap as compared to the conjugatedstructure. Thus, the condensed-cyclic compound of Formula 1 may beusefully used as a blue light-emitting material due to the wide band gapeffected by an appropriate conjugation state.

When an organic light-emitting diode (OLED) including thecondensed-cyclic compound of Formula 1 between a pair of electrodes(anode and cathode) is operated, the OLED may exhibit excellent drivingvoltage, efficiency, brightness and life-time characteristics since thecondensed-cyclic compound of Formula 1 has high heat resistance toJoule's heat generated between organic layers positioned between thepair of electrodes or between one of the organic layers and one of theelectrodes.

The condensed-cyclic compound of Formula 1 may be used between a pair ofelectrodes of an OLED. For example, the condensed-cyclic compound ofFormula 1 may be used as a light-emitting material, but is not limitedthereto.

According to another embodiment of the present invention, there isprovided an OLED including a first electrode, a second electrode facingthe first electrode, and an organic layer interposed between the firstelectrode and the second electrode, wherein the organic layer includesat least one of the condensed-cyclic compound of Formula 1 describedabove.

The organic layer may include at least one of the condensed-cycliccompound of Formula 1. For example, an OLED manufactured according toExample 1, which will be described later, includes only Compound 1(acting as a blue dopant) as the condensed-cyclic compound of Formula 1.Alternatively, an emission layer of the OLED may include Compounds 1 and3 (acting as a blue dopant) as the condensed-cyclic compound ofFormula 1. That is, various modifications are possible in thisembodiment. As used herein, the expression “the organic layer mayinclude at least one of the condensed-cyclic compound of Formula 1” maybe easily understood by one of ordinary skill in the art with referenceto the above description.

The organic layer may include at least one of a hole injection layer(HIL), a hole transport layer (HTL), a functional layer having holeinjection and hole transport abilities, an electron blocking layer(EBL), an emission layer (EML), a hole blocking layer (HBL), an electrontransport layer (ETL), an electron injection layer (EIL), and afunctional layer having electron transport and electron injectionabilities.

For example, the organic layer may have, but is not limited to, aHIL/HTL/EML/ETL/EIL structure or a functional layer having holeinjection and hole transport abilities/EML/ETL/EIL structure.

The term “organic layer” used herein refers to a single layer ormultiple layers interposed between the first electrode and the secondelectrode and may include a metal complex in addition to an organicmaterial.

For example, the organic layer may include an EML including thecondensed-cyclic compound of Formula 1. In other words, thecondensed-cyclic compound of Formula 1 may be used as a light-emittingmaterial. In this regard, the EML may further include a host and thecondensed-cyclic compound of Formula 1 included in the EML may serve asa dopant.

The EML may be a red, green or blue EML. For example, the EML may be ablue EML. In this regard, the condensed-cyclic compound of Formula 1 isused as a blue dopant, whereby an OLED including the condensed-cycliccompound of Formula 1 may have high efficiency, brightness and colorpurity and long lifetime.

FIG. 1 is a schematic cross-sectional view of an OLED according to anembodiment of the present invention. Hereinafter, a structure andmanufacturing method of an OLED will be described in more detail withreference to FIG. 1. The OLED includes a substrate 10, a first electrode20, a HIL 30, a HTL 40, an EML 50, an ETL 60, an EIL 70, and a secondelectrode 80 that are sequentially formed.

First, the substrate 10 may be a substrate used in a general OLED, andmay be a glass substrate or a transparent plastic substrate havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and waterproofness.

The first electrode 20 may be formed by applying a first electrodematerial on the substrate 10 by deposition or sputtering. When the firstelectrode 20 is an anode, the first electrode material may be selectedfrom materials having a high work function so as to facilitate holeinjection. The first electrode 20 may be a reflective electrode or atransparent electrode. Examples of the first electrode material mayinclude indium-tin oxide (ITO), indium-zinc-oxide (IZO), tin oxide(SnO₂), and zinc oxide (ZnO). Also, when magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) is used as the first electrode material, thefirst electrode 20 may be formed as a reflective electrode.

The first electrode 20 may be formed as a single layer or have amulti-layered structure having at least two layers.

An organic layer including the HIL 30, HTL 40, the EML 50, the ETL 60,and the EIL 70 is formed on the first electrode 20 sequentially.

The HIL 30 may be formed on the first electrode 20 by using variousmethods such as vacuum deposition, spin coating, casting, or LBdeposition.

When the HIL 30 is formed by vacuum deposition, the depositionconditions may vary according to a compound used as a material forforming the HIL 30, a structure of a desired HIL, and thermalcharacteristics. For example, the deposition conditions may be, but arenot limited to, a deposition temperature of about 100° C. to about 500°C., a degree of vacuum of about 10⁻⁸ torr to about 10⁻³ torr, and adeposition speed of about 0.01 Å/sec to about 100 Å/sec.

When the HIL 30 is formed by spin coating, the coating conditions mayvary according to a compound used as a material for forming the HIL 30,a structure of a desired HIL, and thermal characteristics. For example,the coating conditions may be, but are not limited to, a coating speedof about 2,000 rpm to about 5,000 rpm and a heat treatment temperaturefor removing a solvent after coating of about 80° C. to about 200° C.

The material for forming the HIL 30 may be a known hole injectionmaterial. Examples of the known hole injection material include, but arenot limited to,N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound such as copper phthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4′4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine (2T-NATA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (PANI/CSA), andpolyaniline/poly(4-styrenesulfonate) (PANI/PSS).

The thickness of the HIL 30 may be in the range of about 100 Å to about10,000 Å. In some embodiments, the thickness of the HIL 30 may be in therange of about 100 Å to about 1,000 Å. When the thickness of the HIL 30is within these range, satisfactory hole injection properties may beobtained without a substantial increase in driving voltage.

Next, the HTL 40 may be formed on the HIL 30 by using various methodssuch as vacuum deposition, spin coating, casting, or LB deposition. Whenthe HTL 40 is formed by vacuum deposition or spin coating, thedeposition and coating conditions may vary according to used compounds.However, in general, the deposition and coating conditions may be almostthe same as the conditions for forming the HIL 30.

A material for forming the HTL 40 may be a known hole transportingmaterial. Examples of the known hole transporting material include, butare not limited to, carbazole derivatives such as N-phenylcarbazole andpolyvinylcarbazole,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), andN,N′-di-1-naphthyl-N,N′-diphenyl-1,1′-biphenyl-4,4′diamine (NPD).

The thickness of the HTL 40 may be in the range of about 50 Å to about2,000 Å. In some embodiments, the thickness of the HTL 40 may be in therange of about 100 Å to about 1,500 Å. When the thickness of the HTL 40is within these ranges, satisfactory hole transport properties may beobtained without a substantial increase in driving voltage.

In addition, the functional layer having hole injection and holetransport abilities may be formed instead of the HIL and the HTL. Amaterial for forming the functional layer having hole injection and holetransport abilities may be selected from known materials.

At least one of the HIL, the HTL, and the functional layer having holeinjection and hole transport abilities may further include acharge-generating material so as to increase the conductivity of thelayers, in addition to the known hole injection material, the known holetransport material and/or the material for forming the functional layerhaving hole injection and hole transport abilities.

The charge-generating material may be, for example, a p-dopant. Examplesof the p-dopant may include, but are not limited to, quinone derivativessuch as tetra-cyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4TCNQ); metaloxides such as an tungsten oxide and a molybdenum oxide; andcyano-containing compounds such as Compound 200 below and the like.

When the HIL, the HTL or the functional layer having hole injection andhole transport abilities further include the charge-generating material,the charge-generating material may be homogeneously or inhomogeneouslydispersed in these layers.

The EML 50 may be formed on the HTL 40 (or the functional layer havinghole injection and hole transport abilities, optionally) by vacuumdeposition, spin coating, casting, or LB deposition. When the EML 50 isformed by vacuum deposition or spin coating, the deposition and coatingconditions may vary according to used compounds. However, in general,the conditions may be almost the same as the conditions for forming theHIL 30.

A material for forming the EML 50 may be at least one of thecondensed-cyclic compound of Formula 1 and a known light-emittingmaterial (host and/or dopant). For example, the EML 50 may include aknown host and the condensed-cyclic compound of Formula 1 as a dopant.In this regard, the condensed-cyclic compound of Formula 1 may act as ablue dopant.

Examples of the known host may include, but are not limited to,Tris(8-hydroxyquinolinato)aluminium (Alq3),4,4′-N,N′-dicabazole-biphenyl (CBP), poly(n-vinylcabazole) (PVK),9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA,1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), E3, anddistyrylarylene (DSA).

Alternatively, the host may be an anthracene-based compound representedby Formula 60 below:

In Formula 60, Ar₁₁ and Ar₁₂ may be each independently a substituted orunsubstituted C₆-C₆₀ arylene group; Ar₁₃ and Ar₁₄ may be eachindependently a substituted or unsubstituted C₁-C₁₀ alkyl group or asubstituted or unsubstituted C₆-C₆₀ aryl group; and e and f may be eachindependently an integer of 0 to 5.

For example, in Formula 60, Ar₁₁ and Ar₁₂ may be each independently aphenylene group; or a phenylene group that is substituted with at leastone of a phenyl group, a naphthyl group, and an anthryl group, but arenot limited thereto.

In Formula 60, e and f may be each independently 0, 1, or 2.

In Formula 60, Ar₁₃ and Ar₁₄ may be each independently a C₁-C₁₀ alkylgroup that is substituted with at least one of a phenyl group, anaphthyl group, and an anthryl group; a phenyl group; a naphthyl group;an anthryl group; a pyrenyl group; a phenanthrenyl group; and a phenylgroup, a naphthyl group, an anthryl group, a pyrenyl group, and aphenanthrenyl group that are substituted with at least one of deuterium,a halogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, but are not limitedthereto.

For example, in Formula 60, Ar₁₁ and Ar₁₂ may be each independently aphenylene group; or a phenylene group that is substituted with at leastone of a phenyl group, a naphthyl group, and an anthryl group; e and fmay be each independently 0, 1, or 2; and Ar₁₃ and Ar₁₄ may be eachindependently one selected from a C₁-C₁₀ alkyl group that is substitutedwith at least one of a phenyl group, a naphthyl group, and an anthrylgroup; a phenyl group; a naphthyl group; an anthryl group; a pyrenylgroup; and a phenanthrenyl group, but are not limited thereto.

For example, the anthracene-based compound of Formula 60 may be one ofCompounds BH01 through BH39 below, but is not limited thereto:

Meanwhile, to manufacture a full-color OLED, a red EML and a green EMLmay be further patterned.

In this regard, examples of known red dopants include, but are notlimited to, PtOEP, Ir(piq)₃, and Btp₂Ir(acac).

Examples of known green dopants include, but are not limited to,Ir(ppy)₃ (ppy=phenylpyridine), Ir(ppy)₂(acac), Ir(mpyp)₃, and C545T.

The amount of the dopants in the EML 50 may be generally in the range ofabout 0.01 to about 15 parts by weight based on 100 parts by weight ofthe host, but is not limited thereto.

The thickness of the EML 50 may be in the range of about 100 Å to about1,000 Å. In some embodiments, the thickness of the HIL 30 may be in therange of about 200 Å to about 600 Å. When the thickness of the EML 50 iswithin these ranges, excellent luminescent properties may be obtainedwithout a substantial increase in driving voltage. Next, the ETL 60 isformed on the EML 50 by using various methods such as vacuum deposition,spin coating, or casting. When the ETL 60 is formed by vacuum depositionor spin coating, the deposition and coating conditions may varyaccording to used compounds. However, in general, the deposition andcoating conditions may be almost the same as the conditions for formingthe HIL 30.

A material for forming the ETL 60 may be a known electron transportingmaterial to stably transport electrons injected from a cathode. Examplesof the known electron transporting materials may include, but are notlimited to, a quinoline derivative such as tris(8-quinolinolate)aluminum(Al_(q3)), TAZ, Balq, beryllium bis(benzoquinolin-10-olate (Beb_(q2)),AND, Compound 201 below, and Compound 202 below.

The thickness of the ETL 60 may be in the range of about 100 Å to about1,000 Å. In some embodiment, the thickness of the ETL may be in therange of about 150 Å to about 500 Å. When the thickness of the ETL 60 iswithin these ranges, satisfactory electron transport properties may beobtained without a substantial increase in driving voltage.

In addition, the ETL 60 may include a known electron transportingorganic compound and a metal-containing material.

The metal-containing material may include a Li-complex. Examples of theLi-complex may include lithium quinolate (LiQ) and Compound 203 below:

Also, the EIL 70, which facilitates electron injection from a cathode,may be formed on the ETL 60, and a material for forming the EIL 70 isnot particularly limited.

The material for forming the EIL 70 may include a well-known materialfor forming an EIL, such as LiF, NaCl, CsF, Li₂O, or BaO. The depositionconditions of the EIL may vary according a used compound. However, ingeneral, the conditions may be almost the same as the conditions forforming the HIL 30.

The thickness of the EIL 70 may be in the range of about 1 Å to about100 Å. In some embodiment, the thickness of the ETL may be in the rangeof about 3 Å to about 90 Å. When the thickness of the EIL 70 is withinthese ranges, satisfactory electron injection properties may be obtainedwithout a substantial increase in driving voltage.

The second electrode 80 is formed on the EIL 70. The second electrode 80may be a cathode, which is an electron injection electrode. Here, ametal for forming the second electrode 80 may include a metal having lowwork function, such as metal, an alloy, an electric conducting compound,or a mixture thereof. In particular, the second electrode 80 may beformed as a thin film by using lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),or magnesium-silver (Mg—Ag), thus being transparent. In order to obtaina top-emission type OLED, the second electrode 80 may be formed as atransparent electrode by using ITO or IZO.

The OLED may be used in a display device and a monochrome or white lightillumination device. The display device and the illumination device mayfurther include at least one thin film transistor (TFT), and a firstelectrode of the OLED may contact one of a source electrode and a drainelectrode that are included in the TFT.

An OLED according to an embodiment of the present invention will now bedescribed in more detail with reference to the following Examples. TheseExamples are for illustrative purposes only and are not intended tolimit the scope of the invention.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1 Synthesis Example1-(1) Synthesis of Intermediate 1-a

Intermediate 1-a was synthesized according to Reaction Scheme 1 below:

50 g (194 mmol) of 9-bromo phenanthrene was added to a round-bottomflask containing 500 ml of tetrahydrofuran, and a temperature of theround-bottom flask was then adjusted to be −78° C. in a nitrogenatmosphere. After 30 minutes, 146 ml (233 mmol) of normal butyl lithiumwas slowly dropped to the mixture, 28.3 g (274 mmol) of trimethylboratewas slowly dropped thereto after 1 hour, and the temperature was raisedto room temperature. The resultant mixture was stirred for about 12hours at room temperature and 2N (normal) aqueous hydrochloric acidsolution was dropped to the reaction solution until the solution becomesan acid solution, and the resultant solution was then extracted. Theorganic layer was separated and evaporated under reduced pressure. Theresidue was recrystallized with normal hexane and the resulting productwas filtered and dried. As a result, 35 g of white solid Intermediate1-a (yield: 81%) was obtained.

Synthesis Example 1-(2) Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Reaction Scheme 2 below:

To a round-bottom flask was added 24 g (112 mmol) of methyl2-bromobenzoate, 34.7 g (0.156 mmol) of Intermediate 1-a, 2.6 g (2 mmol)of tetrakistriphenylphosphinpalladium {Pd(PPh₃)₄}, 30.9 g (223 mmol) ofpotassium carbonate, 50 ml of water, 125 ml of toluene, and 125 ml oftetrahydrofuran and the resultant mixture was then refluxed for 12hours. After the reaction was terminated, the reactant was subjected toa layer separation process to obtain an organic layer. The obtainedorganic layer was concentrated under reduced pressure, purified bycolumn and then dried. As a result, 25 g of white solid Intermediate 1-b(yield: 72%) was obtained.

Synthesis Example 1-(3) Synthesis of Intermediate 1-c

Intermediate 1-c was synthesized according to Reaction Scheme 3 below:

25 g (80 mmol) of Intermediate 1-b was added to a round-bottom flaskcontaining 250 ml of tetrahydrofuran, and a temperature of theround-bottom flask was then reduced to −78° C. in a nitrogen atmosphere.After 30 minutes, 150 ml (240 mmol) of 1.6M phenyl lithium was slowlydropped to the mixture and the temperature was raised to roomtemperature after 1 hour. The resultant mixture was stirred at roomtemperature for about 2 hours and an aqueous ammonium chloride solutionwas added thereto. Thereafter, the resulting solution was extracted toobtain an organic layer and the obtained organic layer was thenevaporated under reduced pressure. The residue was recrystallized withnormal hexane and the resulting product was filtered and dried. As aresult, 29 g of white solid Intermediate 1-c (yield: 83%) was obtained.

Synthesis Example 1-(4) Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Reaction Scheme 4 below:

29 g (66 mmol) of Intermediate 1-c was added to a round-bottom flaskcontaining 290 ml of acetic acid. Subsequently, a temperature of theround-bottom flask was raised to 80° C. and 1 to 2 droplets of anaqueous hydrochloric acid solution was added thereto, and the resultantsolution was refluxed for about 2 hours and the temperature was adjustedto room temperature. The solid produced therefrom was filtered anddried. As a result, 27 g of white solid Intermediate 1-d (yield: 93%)was obtained.

Synthesis Example 1-(5) Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Reaction Scheme 5 below:

27 g (65 mmol) of Intermediate 1-d was added to a round-bottom flaskcontaining 216 ml of chloroform and the mixture was stirred.Subsequently, 28.9 g (181 mmol) of bromine was diluted with 54 ml ofchloroform, the diluted mixture was slowly dropped to the stirredmixture, and the resultant mixture was stirred at room temperature for48 hours. Thereafter, solid produced therefrom was filtered and dried.As a result, 27 g of white solid Intermediate 1-e (yield: 93%) wasobtained.

Synthesis Example 1-(6) Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 7 below:

To a round-bottom flask were added 10 g (17 mmol) of Intermediate 1-e,7.6 g (45 mmol) of diphenyl amine, 0.2 g (0.7 mmol) of palladium acetate{Pd(OAc)₂}, 6.7 g (69 mmol) of sodium tertiary butoxide, 0.14 g (0.7mmol) of tri-tertiary butylphosphine, and 100 ml of toluene and themixture was maintained at a reaction temperature of 100° C. for 2 hoursto induce a reaction therebetween. After the reaction was terminated,the reaction solution was filtered, the filtrate was concentrated, andthe resulting filtrate was purified by column chromatography.Thereafter, the resulting product was recrystallized with toluene andmethanol and solid produced therefrom was filtered and dried. As aresult, 5.7 g of Compound 1 was obtained as a pale yellow solid (yield:40%).

The produced compound was identified using NMR.

MS: m/z 752 [M]⁺

¹H NMR (CDCl₃) δ 8.89 (d, 1H), 8.47 (d, 1H), 8.40 (s, 1H), 8.24 (d, 1H),7.73 (t, 1H), 7.63 (m, 2H), 7.27 (m, 23H), 7.01 (m, 10H)

Synthesis Example 2 Synthesis of Compound 3 Synthesis Example 2-(1)Synthesis of Intermediate 2-a

Intermediate 2-a was synthesized according to Reaction Scheme 8 below:

To a round-bottom flask were added 16.3 g (96 mmol) of 4-amino biphenyl,15.8 g (101 mmol) of bromobenzene, 0.32 g (1.4 mmol) of palladiumacetate, 0.9 g (1.4 mmol) of 2,2-bis(diphenylphosphino)-1,1′-binaphthyl,18.5 g (193 mmol) of sodium tertiary butoxide, and 160 ml of toluene andthe mixture was refluxed for 24 hours. After the temperature wasadjusted to be room temperature, the mixture was filtered, the filtratewas concentrated, and the resulting filtrate was purified by columnchromatography. Thereafter, the resulting product was recrystallizedwith dichloromethane and methanol and solid produced therefrom wasfiltered and dried. As a result, 15 g of white solid Intermediate 2-awas obtained (yield: 60%).

Synthesis Example 2-(2) Synthesis of Compound 3

3.7 g of Compound 3 was obtained as a pale yellow solid (yield: 31%) inthe same manner as in Synthesis Example 1-(6), except that Intermediate2-a was used instead of diphenyl amine.

The produced compound was identified using NMR.

MS: m/z 904 [M]⁺

¹H NMR (CDCl₃) δ 8.90 (d, 1H), 8.51 (m, 2H), 8.27 (d, 1H), 7.75 (t, 2H),7.61 (m, 6H), 7.48 (m, 9H), 7.36 (m, 9H), 7.23 (m, 11H), 7.12 (m, 7H)

Synthesis Example 3 Synthesis of Compound 9

4.7 g of Compound 9 was obtained as a pale yellow solid (yield: 39%) inthe same manner as in Synthesis Example 2, except that, in SynthesisExample 2-(1), 4-tertiary-butylaniline was used instead of 4-aminobiphenyl and 1-bromo-4-tertiary-butylbenzene was used instead ofbromobenzene.

The produced compound was identified using NMR.

MS: m/z 977 [M]⁺

¹H NMR (CDCl₃) δ 8.89 (s, 1H), 8.49 (d, 1H), 8.23 (s, 1H), 7.68 (m, 3H),7.31 (m, 21H), 7.05 (m, 9H), 1.38 (s, 18H), 1.37 (s, 18H)

Synthesis Example 4 Synthesis of Compound 10

2.7 g of Compound 10 was obtained as a pale yellow solid (yield: 24%) inthe same manner as in Synthesis Example 2, except that, in SynthesisExample 2-(1), 4-tertiary-butylaniline was used instead of 4-aminobiphenyl and bromobenzene-d₅ was used instead of bromobenzene.

The produced compound was identified using NMR.

MS: m/z 875 [M]⁺

¹H NMR (CDCl₃) δ 8.91 (d, 1H), 8.45 (m, 2H), 8.26 (d, 1H), 7.67 (m, 3H),7.30 (m, 15H), 7.07 (m, 6H)

Synthesis Example 5 Synthesis of Compound 11

6.4 g of Compound 11 was obtained as a pale yellow solid (yield: 67%) inthe same manner as in Synthesis Example 2, except that, in SynthesisExample 2-(1), 4-tertiary-butylaniline was used instead of 4-aminobiphenyl and 1-bromo-4-(trimethylsilyl)benzene was used instead ofbromobenzene.

The produced compound was identified using NMR.

MS: m/z 1009 [M]⁺

¹H NMR (CDCl₃) δ 8.88 (d, 1H), 8.51 (d, 1H), 8.43 (S, 1H), 8.24 (d, 1H),7.73 (t, 1H), 7.64 (m, 2H), 7.21 (m, 29H), 1.36 (s, 9H), 1.35 (S, 9H),0.30 (s, 9H), 0.29 (s, 9H)

Synthesis Example 6 Synthesis of Compound 12

5.1 g of Compound 12 was obtained as a pale yellow solid (yield: 49%) inthe same manner as in Synthesis Example 2, except that1-bromo-4-tertiary-butylbenzene was used instead of bromobenzene inSynthesis Example 2-(1).

The produced compound was identified using NMR.

MS: m/z 1017 [M]⁺

¹H NMR (CDCl₃) δ 8.93 (s, 1H), 8.50 (m, 2H), 8.29 (d, 1H), 7.40 (m,42H), 1.41 (s, 9H), 1.40 (s, 9H)

Synthesis Example 7 Synthesis of Compound 28

3.3 g of Compound 28 was obtained as a pale yellow solid (yield: 38%) inthe same manner as in Synthesis Example 1, except that methyl magnesiumbromide was used instead of phenyl lithium in Synthesis Example 1-(3).

The produced compound was identified using NMR.

MS: m/z 628 [M]⁺

¹H NMR (CDCl₃) δ 8.84 (s, 1H), 8.53 (m, 2H), 8.26 (s, 2H), 7.42 (m,25H), 1.75 (s, 6H)

Synthesis Example 8 Synthesis of Compound 29

3.3 g of Compound 29 was obtained as a pale yellow solid (yield: 38%) inthe same manner as in Synthesis Example 1, except that methyl magnesiumbromide was used instead of phenyl lithium in Synthesis Example 1-(3)and Intermediate 2-a was used instead of diphenyl amine in SynthesisExample 1-(6).

The produced compound was identified using NMR.

MS: m/z 780 [M]⁺

¹H NMR (CDCl₃) δ 8.85 (s, 1H), 8.55 (m, 2H), 8.28 (s, 2H), 7.47 (m,33H), 1.76 (s, 6H)

Synthesis Example 9 Synthesis of Compound 14 Synthesis Example 9-(1)Synthesis of Intermediate 9-a

Intermediate 9-a was synthesized according to Reaction Scheme 9 below:

To a 1 L round-bottom flask were added 30 g (111.56 mmol) of2,4-dibromo-6-fluoroaniline, 31.2 g (245.44 mmol) of phenylboronicacid-d₅, 61.9 g (446.27 mmol) of potassium carbonate, 2.6 g (2.20 mmol)of tetrakistriphenylphosphinpalladium, 120 ml of water, 300 ml oftoluene, and 300 ml of tetrahydrofuran and the mixture was maintained ata reaction temperature of 80° C. for 24 hours to induce a reactiontherebetween. After the reaction was terminated, the reaction productwas subjected to a layer separation process to remove a water layer andseparate an organic layer therefrom, and the obtained organic layer wasconcentrated under reduced pressure. The resulting product was purifiedby column chromatography by using hexane and dichloromethane and solidproduced therefrom was dried. As a result, 24.2 g of white solidIntermediate 9-a was obtained (yield: 79.4%).

Synthesis Example 9-(2) Synthesis of Intermediate 9-b

Intermediate 9-b was synthesized according to Reaction Scheme 10 below:

To a round-bottom flask were added 15 g (55 mmol) of Intermediate 9-a,8.9 g (55 mmol) of bromobenzene-d₅, 0.25 g (1.1 mmol) of palladiumacetate, 0.68 g (1.1 mmol) of2,2-bis(diphenylphosphino)-1,1′-binaphthyl, 10.6 g (110 mmol) of sodiumtertiary butoxide, and 150 ml of toluene and the mixture was refluxedfor 24 hours. The resultant mixture was filtered, the filtrate wasconcentrated, and the resulting filtrate was purified by columnchromatography. Thereafter, the resulting product was recrystallizedwith dichloromethane and methanol and solid produced therefrom wasfiltered and dried. As a result, 14 g of white solid Intermediate 9-bwas obtained (yield: 72%).

Synthesis Example 9-(3) Synthesis of Compound 14

3.1 g of Compound 14 was obtained as a pale yellow solid (yield: 24%) inthe same manner as in Synthesis Example 1, except that Intermediate 9-bwas used instead of diphenyl amine in Synthesis Example 1-(6).

The produced compound was identified using NMR.

MS: m/z 1123 [M]⁺

¹H NMR (CDCl₃) δ 8.81 (s, 1H), 8.35 (d, 1H), 8.05 (s, 2H), 7.71 (t, 2H),7.34 (m, 16H), 6.84 (d, 2H)

Synthesis Example 10 Synthesis of Compound 17

4.3 g of Compound 17 was obtained as a pale yellow solid (yield: 42%) inthe same manner as in Synthesis Example 2, except that 4-cyanoanilinewas used instead of 4-amino biphenyl in Synthesis Example 2-(1).

The produced compound was identified using NMR.

MS: m/z 803 [M]⁺

¹H NMR (CDCl₃) δ 8.90 (d, 1H), 8.51 (m, 2H), 8.33 (d, 1H), 7.74 (m, 3H),7.25 (m, 29H), 6.93 (d, 2H)

Synthesis Example 11 Synthesis of Compound 22 Synthesis Example 11-(1)Synthesis of Intermediate 11-a

Intermediate 11-a was synthesized according to Reaction Scheme 11 below:

To a reactor were added 50 g (197 mmol) of 1,3-dibromo-5-fluorobenzene,28.8 g (167 mmol) of 1-naphthyl boronic acid, 4.6 g (3.9 mmol) oftetrakistriphenylphosphinpalladium, 54.4 g (394 mmol) of potassiumcarbonate, 450 ml of toluene, and 150 ml of water and the mixture wasrefluxed. After the reaction was terminated, the resultant mixture wasextracted to separate an organic layer. Thereafter, the organic layerwas evaporated under reduced pressure and purified by columnchromatography. As a result, 25 g of Intermediate 11-a was obtained in atransparent liquid state (yield: 42%).

Synthesis Example 11-(2) Synthesis of Intermediate 11-b

Intermediate 11-b was synthesized according to Reaction Scheme 12 below:

Intermediate 11-b was synthesized in the same manner as in SynthesisExample 2-(1), except that 4-tert-butylaniline was used instead of4-amino biphenyl and Intermediate 11-a was used instead of bromobenzene.

Synthesis Example 11-(3) Synthesis of Compound 22

1.6 g of Compound 22 was obtained as a pale yellow solid (yield: 21%) inthe same manner as in Synthesis Example 1, except that Intermediate 11-bwas used instead of diphenyl amine in Synthesis Example 1-(6).

The produced compound was identified using NMR.

MS: m/z 1153 [M]⁺

¹H NMR (CDCl₃) δ 8.88 (d, 1H), 8.56 (m, 2H), 8.28 (d, 1H), 7.88 (m, 6H),7.71 (m, 3H), 7.30 (m, 30H), 6.86 (m, 5H), 1.35 (s, 9H), 1.34 (s, 9H)

Synthesis Example 12 Synthesis of Compound 26

2.7 g of Compound 26 was obtained as a pale yellow solid (yield: 36%) inthe same manner as in Synthesis Example 1, except that9,9-dimethyl-N-phenyl-9H-fluoren-2-amine was used instead of diphenylamine in Synthesis Example 1-(6).

The produced compound was identified using NMR.

MS: m/z 985 [M]⁺

¹H NMR (CDCl₃) δ 8.89 (s, 1H), 8.37 (m, 3H), 7.64 (m, 7H), 7.24 (m,33H), 1.42 (s, 6H), 1.36 (s, 6H)

Synthesis Example 13 Synthesis of Compound 54

3.3 g of Compound 54 was obtained as a pale yellow solid (yield: 37%) inthe same manner as in Synthesis Example 2, except that2-bromo-9,9-dimethyl-9H-fluorene was used instead of bromobenzene inSynthesis Example 2-(1).

The produced compound was identified using NMR.

MS: m/z 1013 [M]⁺

¹H NMR (CDCl₃) δ 8.86 (s, 1H), 8.50 (d, 1H), 8.30 (s, 2H), 7.53 (m,39H), 1.76 (s, 6H), 1.49 (s, 12H)

Synthesis Example 14 Synthesis of Compound 64 Synthesis Example 14-(1)Synthesis of Intermediate 14-a

Intermediate 14-a was synthesized according to Reaction Scheme 13 below:

To a reactor were added 500 ml of acetic acid and 120 g (1.39 mol) of3-methyl-2-butanone and the temperature was raised to 60° C.Subsequently, 150 g (1.39 mol) of phenylhyrazine was slowly added to themixture and the resultant mixture was refluxed. After the reaction wasterminated, 500 ml of water was added to the mixture and the mixture wasneutralized with sodium hydroxide. The resultant mixture was extractedseveral times with ethyl acetate and the obtained organic layer wasevaporated under reduced pressure and the residue was purified by columnchromatography. As a result, 156 g of Intermediate 14-a was obtained(yield: 71%).

Synthesis Example 14-(2) Synthesis of Intermediate 14-b

Intermediate 14-b was synthesized according to Reaction Scheme 14 below:

100 g (0.628 mol) of Intermediate 14-a and 500 ml of acetic acid wereadded to a reactor. Subsequently, 118 g (1.88 mol) of sodiumcyanoborohydride was slowly added to the mixture so as not to incursevere heat generation. The resultant mixture was stirred for 5 hours,300 ml of water was added thereto, and the mixed solution was made basicwith sodium hydroxide. Thereafter, ethyl acetate was added to theresultant solution, the solution was extracted several times to separatean organic layer, and the obtained organic layer was concentrated. Theresulting product was then purified by column chromatography. As aresult, 55 g of Intermediate 14-b was obtained (yield: 54%).

Synthesis Example 14-(3) Synthesis of Compound 64

1.8 g of Compound 64 was obtained as a pale yellow solid (yield: 34%) inthe same manner as in Synthesis Example 1, except that Intermediate 14-bwas used instead of diphenyl amine in Synthesis Example 1-(6).

The produced compound was identified using NMR.

MS: m/z 737 [M]⁺

¹H NMR (CDCl₃) δ 8.90 (s, 1H), 8.76 (d, 1H), 8.57 (s, 1H), 8.43 (d, 1H),7.78 (m, 3H), 7.16 (m, 21H), 4.01 (s, 1H), 3.83 (s, 1H), 1.37 (s, 3H),1.35 (s, 3H), 1.26 (m, 6H), 1.14 (m, 6H)

Synthesis Example 15 Synthesis of Compound 68 Synthesis Example 15-(1)Synthesis of Intermediate 15-a

Intermediate 15-a was synthesized according to Reaction Scheme 15 below:

To a 500 ml round-bottom flask were added 50 g (0.462 mol) ofphenylhydrazine and 170 ml of acetic acid and a temperature of the flaskwas raised to 60° C. Subsequently, 51.9 g (0.462 mol) of2-methylcyclohexanone was added to the heated round-bottom flask. Afterthe addition of the compound was terminated, the mixture was refluxedfor 8 hours. After the reaction was terminated, 100 ml of water wasadded to the mixture and the resultant mixture was made basic withsodium hydroxide.

The resulting solution was extracted with water and ethyl acetate toseparate an organic layer. The obtained organic layer was subjected toanhydrous treatment with magnesium sulfate and concentrated underreduced pressure. Thereafter, the resulting product was purified bycolumn chromatograph by using hexane and ethyl acetate as a developingsolvent. As a result, 72 g of Intermediate 15-a was obtained (yield:84%).

Synthesis Example 15-(2) Synthesis of Intermediate 15-b

Intermediate 15-b was synthesized according to Reaction Scheme 16 below:

57 g (0.308 mol) of Intermediate 15-a obtained according to ReactionScheme 15 was dissolved in 570 ml of toluene in a 2 L round-bottom flaskwith a nitrogen atmosphere, and the temperature was then reduced to −10°C. Subsequently, 300 ml (0.474 mol) of 1.6M methyllithium was slowlyadded to the solution and maintained at −10° C. for 3 hours to induce areaction therebetween. After the reaction was terminated, water wasslowly added to the reaction solution until the solution had noreactivity.

The resulting solution was extracted with water and ethyl acetate toseparate an organic layer. The obtained organic layer was subjected toanhydrous treatment with magnesium sulfate and concentrated underreduced pressure. Thereafter, the resulting product was purified bycolumn chromatograph by using hexane and ethyl acetate as a developingsolvent. As a result, 47 g of Intermediate 15-b was obtained (yield:76%).

Synthesis Example 15-(3) Synthesis of Intermediate 15-c

Intermediate 15-b was synthesized according to Reaction Scheme 17 below:

To a 1 L round-bottom flask were added 40 g (0.199 mol) of Intermediate15-b obtained according to Reaction Scheme 16, 48.6 g (0.238 mol) ofiodobenzene, 0.89 g (0.004 mol) oftris(dibenzylideneacetone)dipalladium(0), 2.47 g (0.004 mol) of2,2-bis(diphenylphosphino)-1,1′-binaphthyl, 38.19 g (0.397 mol) ofsodium tertiarybutoxide, and 400 ml of toluene and the mixture wasrefluxed for 8 hours. After the reaction was terminated, the resultingmixture was filtered with celite, and the filtrate was concentratedunder reduced pressure. The resulting product was purified by columnchromatography using hexane as a developing solvent. As a result, 44 gof Intermediate 15-c was obtained (yield: 79%).

Synthesis Example 15-(4) Synthesis of Intermediate 15-d

Intermediate 15-d was synthesized according to Reaction Scheme 18 below:

Intermediate 15-c Intermediate 15-d

To a 500 ml round-bottom flask were added 44 g (0.158 mol) ofIntermediate 15-c obtained according to Reaction Scheme 17 and 130 ml ofdimethylformamide and the temperature was reduced to 0° C. Subsequently,25.2 g (0.142 mol) of N-bromosuccinimide was dissolved in 200 ml ofdimethylformamide and the solution was slowly added to the mixture.After the addition of the solution was terminated, the temperature wasraised to room temperature and the resulting solution was stirred for 2hours.

After the reaction was terminated, the resultant solution was extractedwith water and dichloromethane to separate an organic layer. Theobtained organic layer was subjected to anhydrous treatment withmagnesium sulfate and concentrated under reduced pressure. Thereafter,the resulting product was crystallized with hexane and crystal producedtherefrom was filtered. As a result, 45 g of Intermediate 15-d wasobtained (yield: 80%).

Synthesis Example 15-(5) Synthesis of Intermediate 15-e

Intermediate 15-e was synthesized according to Reaction Scheme 19 below:

To a 1 L round-bottom flask were added 40 g (0.112 mol) of Intermediate15-d obtained according to Reaction Scheme 18, 34 g (0.134 mol) ofbis(pinacolato)diboron, 2.73 g (0.003 mol) of palladium(II)chloride-1-,1′-bis(diphenylphosphino)ferrocene, 32.9 g (0.335 mol) ofpotassium acetate, and 480 ml of toluene and the mixture was refluxedfor 8 hours. After the reaction was terminated, the resultant mixturewas filtered with celite and the filtrate was concentrated under reducedpressure. Thereafter, the resulting product was purified by columnchromatography by using hexane and ethyl acetate as a developingsolvent. As a result, 26 g of Intermediate 15-e was obtained (yield:58%).

Synthesis Example 15-(6) Synthesis of Compound 68

To a round-bottom flask were added 5.0 g (9 mmol) of Intermediate 15-e,8.4 g (2.1 mmol) of Intermediate 1-e, 0.4 g (0.3 mmol) oftetrakistriphenylphosphinpalladium, 3.6 g (26 mmol) of potassiumcarbonate, 25 ml of 1,4-dioxane, 25 ml of toluene, and 10 ml of water,and the mixture was refluxed. After the reaction was terminated, waterand hexane were added to the resultant mixture. Crystals producedtherefrom were filtered. The crystals were recrystallized to obtain 5.3g of Compound 68 (yield: 57%).

The produced compound was identified using NMR.

MS: m/z 969 [M]⁺

¹H NMR (CDCl₃) δ 9.07 (d, 1H), 8.95 (m, 2H), 8.48 (d, 1H), 7.75 (m, 6H),7.37 (m, 24H), 6.62 (s, 2H), 2.00 (m, 2H), 1.60 (m, 14H), 1.30 (s, 3H),1.28 (s, 3H), 1.18 (s, 3H), 1.15 (s, 3H)

Example 1

ITO glass was patterned to have an emission area of 2 mm×2 mm and thenwashed. The ITO glass was placed in a vacuum chamber, CuPc was depositedon the ITO glass at a base pressure of 1×10⁻⁷ torr to form a HIL havinga thickness of 800 Å, and α-NPD was deposited on the HIL to form a HTLhaving a thickness of 300 Å. Compound BH01 and Compound 1 (3 wt %) wereco-deposited on the HTL to form an EML having a thickness of 250 Å andAlq₃ was deposited on the EML to form an ETL having a thickness of 350Å. Thereafter, a LiF EIL having a thickness of 5 Å was formed on the ETLand an Al electrode having a thickness of 500 Å was formed on the EIL,thereby completing the manufacturing of an OLED.

Examples 2 Through 8

OLEDs were manufactured in the same manner as in Example 1, except thatCompounds 3, 9, 10, 11, 12, 28, and 29 were respectively used instead ofCompound 1.

Comparative Example 1

An OLED was manufactured in the same manner as in Example 1, except thatCompound A below was used instead of Compound 1.

Comparative Example 2

An OLED was manufactured in the same manner as in Example 1, except thatCompound B below was used instead of Compound 1.

Evaluation Example 1

Driving voltage, current, luminance (measured at 0.4 mA), colorcoordinate, and lifetime (T80) of each of the OLEDs manufacturedaccording to Examples 1 through 8 and Comparative Examples 1 and 2 weremeasured using PR650 Spectroscan Source Measurement Unit (manufacturedby PhotoResearch), and the measurement results are shown in Table 1below. In addition, lifetime data of the OLEDs are illustrated in FIGS.2 and 3 and current density date of the OLEDs are illustrated in FIGS. 4and 5. T80 indicates the time at which the luminance of each of theOLEDs is decreased to 80% of the initial luminance and it was measuredat 3,000 nit.

TABLE 1 Current External Vol. density quantum Luminance T80 dopant (V)(mA/cm²) efficiency (cd/m²) CIEx CIEy (hr) Example 1 1 4.0 10 5.61 4710.145 0.096 187 Example 2 3 3.6 10 6.83 690 0.142 0.123 379 Example 3 93.8 10 6.09 695 0.141 0.148 257 Example 4 10 3.8 10 6.33 624 0.143 0.120207 Example 5 11 4.0 10 6.71 677 0.142 0.125 180 Example 6 12 3.8 106.16 693 0.141 0.145 211 Example 7 28 3.8 10 5.43 480 0.145 0.103 150Example 8 29 3.9 10 6.46 663 0.141 0.127 194 Comparative A 4.3 10 5.06534 0.133 0.137 45 Example 1 Comparative B 4.3 10 4.59 504 0.134 0.14435 Example 2

From the results as shown in Table 1 and FIGS. 2 through 5, it isconfirmed that each of the OLEDs of Examples 1 through 8 has excellentdriving voltage and external quantum efficiency, higher luminance,higher color purity, and longer lifetime, as compared to the OLEDs ofComparative Examples 1 and 2.

As described above, the condensed-cyclic compound of Formula 1 may havehigh thermal resistance and excellent luminous properties, and thus anOLED including the condensed-cyclic compound of Formula 1 may haveexcellent driving voltage, high efficiency, high luminance, excellentexternal quantum efficiency, and long lifetime.

Synthesis Example 21 Synthesis of Compound 2A Synthesis Example 21-(1)Synthesis of [Intermediate 2A-a]

1-bromo-2-iodobenzene (31.7 g, 112 mmol), 9-phenanthrilboronic acid(34.6 g, 156 mmol), tetrakistriphenylphosphinepalladium (2.6 g, 2 mmol),potassium carbonate (30.9 g, 223 mmol), 50 mL of water, 125 mL oftoluene, and 125 mL of tetrahydrofurane were loaded into a round-bottomflask, and then, the mixture was refluxed for 12 hours. Once an organiclayer was concentrated under reduced pressure, the resultant wassubjected to column chromatography to obtain 26.9 g (yield of 72%) of[Intermediate 2A-a].

Synthesis Example 21-(2) Synthesis of [Intermediate 2A-b]

[Intermediate 2A-a] (4.1 g, 12.2 mmol) was added to 50 mL oftetrahydrofurane, and then, at a temperature of −78° C., n-butyllithium(5.8 mL, 14.6 mmol) was added dropwise thereto. The resultant wasstirred for about 1 hour. Then, at the same temperature, 9-fluorenone(1.9 g, 10.8 mmol) dissolved in 10 mL of tetrahydrofurane was slowlyadded dropwise thereto and the resultant was stirred for 2 hours, andthen, stirred for 12 hours at room temperature. After extraction usingethyl acetate, the resultant was recrystallized by using diethylether toobtain 4.2 g (yield of 79%) of [Intermediate 2A-b].

Synthesis Example 21-(3) Synthesis of [Intermediate 2A-c]

[Intermediate 2A-b] (28.8 g, 66.3 mmol) was added to 300 mL of an aceticacid, and then, the temperature was raised to 80° C. and one or twodrops of an HCl aqueous solution were added thereto, followed by twohours of refluxing. The temperature was dropped to room temperature, andthe resultant was filtered to obtain 25.4 g (yield of 92%) of[Intermediate 2A-c].

Synthesis Example 21-(4) Synthesis of [Intermediate 2A-d]

[Intermediate 2A-c] (22.9 g, 0.055 mol) was added to 250 mL ofdimethylformamide, and the resultant was stirred at a temperature of 0°C. n-bromosuccinimide (21.5 g, 0.121 mol) dissolved in 70 mL ofdimethylformamide was added dropwise thereto, and the resultant wasstirred for 12 hours. The reaction product was filtered by usingdistilled water and washed with hexane. Then, the resultant wasdissolved in dichloromethane and heated, and then, subjected to anactive charcoal treatment with acid white clay. Then, the resultant waswashed with dichloromethane and re-crystallized by using hexane, therebyobtaining 23.7 g (yield of 75%) of [Intermediate 2A-d].

Synthesis Example 21-(5) Synthesis of [Intermediate 2A-e]

(4-chlorophenyl)trimethylsilane (18.5 g, 0.1 mol),4-amino-tertiarybutylbenzene (14.9 g, 0.1 mol), palladium acetate (0.08g, 0.32 mmol), 2,2′-bis(diphenylphosphino)-1-1′-binaphthyl (0.26 g, 0.42mmol), and sodium tertiarybutoxide (15.2 g, 0.16 mol) were added to 150mL of toluene, and the mixture was refluxed for 12 hours. The resultantwas cooled to room temperature, and then, washed by using methanol andre-crystallized by using dichloromethane and methanol, thereby obtaining22.3 g (yield of 75%) of [Intermediate 2A-e].

Synthesis Example 21-(6) Synthesis of [Compound 2A]

[Intermediate 2A-d] (5.5 g, 9.5 mmol), [Intermediate 1-e] (7.4 g, 24.8mmol), and palladium acetate (0.15 g, 0.67 mmol) were added to 80 mL oftoluene, and the mixture was stirred at a temperature of 60° C.Tritertiarybutylphosphine (0.42 g, 1.9 mmol) and potassium tertiarybutoxide (4.2 g, 38.1 mmol) were slowly added dropwise thereto, andthen, reacted at a temperature of 100° C. for 2 hours. The reactionproduct was subjected to an extraction process using dichloromethane,followed by column chromatography, thereby obtaining 4.1 g (yield of43%) of [Compound 2A].

MS (MALDI-TOF): m/z 1006.51 [M]⁺

Synthesis Example 22 Synthesis of Compound 6A Synthesis Example 22-(1)Synthesis of Intermediate 6A-a

4-amino biphenyl (16.3 g, 96 mmol), bromobenzene (15.8 g, 101 mmol),palladium acetate (0.32 g, 1.4 mmol), 2,2-bisdiphenylphosphino-1,1′-binaphthyl (0.9 g, 1.4 mmol), sodium tertiarybutoxide (18.5 g, 193 mmol), and 160 ml of toluene were added to around-bottom flask, and then, the mixture was refluxed for 24 hours. Thetemperature was adjusted to be room temperature, and then, the resultantwas filtered and the obtained filtrate was concentrated and purified bycolumn chromatography. Thereafter, the resultant was re-crystallized byusing dichloromethane and methanol, and filtered and dried, therebyproducing 15 g (yield of 60%) of [Intermediate 6A-a], which was in theform of white solid.

Synthesis Example 22-(2) Synthesis of [Compound 6A]

[Compound 6A] (yield of 45%) was obtained in the same manner as inSynthesis Example 21-(6), except that [Intermediate 6A-a] was usedinstead of [Intermediate 2A-e].

MS (MALDI-TOF): m/z 902.37 [M]⁺

Synthesis Example 23 Synthesis of Compound 8A

[Compound 8A] (yield of 47%) was obtained in the same manner as inSynthesis Example 21-(5), except that pentadeuterated iodobenzene wasused instead of (4-chlorophenyl)trimethylsilane.

MS (MALDI-TOF): m/z 872.49 [M]⁺

Synthesis Example 24 Synthesis of Compound 18A

[Compound 18A] (yield of 44%) was obtained in the same manner as inSynthesis Example 21, except that, in Synthesis Example 21-(5),1-cyano-4-chlorobenzene was used instead of(4-chlorophenyl)trimethylsilane, and 2-methyl-5-aminopyridine was usedinstead of 4-amino-tertiarybutylbenzene.

MS (MALDI-TOF): m/z 830.32 [M]⁺

Example 21

ITO glass was patterned such that an emission area thereof was a size of2 mm×2 mm, and then, washed. The ITO glass was mounted on a vacuumchamber, and then, a base pressure was adjusted to be 1×10⁻⁷ torr. Then,CuPc was deposited on the ITO glass to form a hole injection layerhaving a thickness of 800 Å, and α-NPD was deposited on the holeinjection layer to form a hole transport layer having a thickness of 300Å. Compound BH1 and Compound 2A (3 wt. %) were co-deposited on the holetransport layer to form an emission layer having a thickness of 250 Å,and then, Alq₃ was deposited on the emission layer to form an electrontransport layer having a thickness of 350 Å. Subsequently, LiF electroninjection layer having a thickness of 5 Å and Al electrode having athickness of 500 Å were sequentially formed thereon, thereby completingthe manufacture of an organic light-emitting diode.

Examples 22 to 24

Organic light-emitting diodes were manufactured in the same manner as inExample 21, except that Compounds 6A, 8A, and 18A were used instead ofCompound 2A.

Evaluation Example 2

Driving voltage, current, luminance (measured at 0.4 mA), colorcoordinate, and lifetime (T80) of the organic light-emitting diodesmanufactured according to Examples 21 to 24 and Comparative Examples 1and 2 were measured by using PR650 Spectroscan Source Measurement Unit.(a product of PhotoResearch Company), and results thereof are shown inTable 2. T80 indicates a period of time that has elapsed when luminancereduces to 80% of the initial luminance, and herein, was measured at3,000 nit.

TABLE 2 Current External Voltage density quantum Luminance T80 Dopant(V) (mA/cm²) efficiency (cd/m²) CIEx CIEy (hr) Example 21 2A 3.6 10 7.67645 0.142 0.112 412 Example 22 6A 3.6 10 7.12 674 0.142 0.120 397Example 23 8A 3.7 10 6.99 661 0.141 0.118 378 Example 24 18A  3.7 106.56 624 0.141 0.121 325 Comparative A 4.3 10 5.06 534 0.133 0.137 45Example 1 Comparative B 4.3 10 4.59 504 0.134 0.144 35 Example 2

From the results as shown in Table 2, it is confirmed that each of theOLEDs of Examples 21 through 24 has excellent driving voltage andexternal quantum efficiency, higher luminance, higher color purity, andlonger lifetime, as compared to the OLEDs of Comparative Examples 1 and2.

While the present invention has been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeof the present invention as defined by the following claims.

What is claimed is:
 1. A condensed-cyclic compound represented byFormula 1A below:

wherein R₁ is represented by —(Ar₁)_(a1)—(R₁₁)_(b1), R₂ is representedby —(Ar₂)_(a2)—(R₁₂)_(b2), R₃ is represented by —(Ar₃)_(a3)—(R₁₃)_(b3),and R₄ is represented by —(Ar₄)_(a4)—(R₁₄)_(b4); Ar₁ through Ar₄ areeach independently a substituted or unsubstituted C₆-C₆₀ aromaticlinking group or a substituted or unsubstituted C₂-C₆₀ heteroaromaticlinking group; Ar₅ and Ar₆ are each independently a substituted orunsubstituted C₆-C₆₀ arylene group or a substituted or unsubstitutedC₂-C₆₀ heteroarylene group; R₁₁ through R₁₄ are each independentlynon-covalent electron pairs, hydrogen, deuterium, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group,a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, or a substituted or unsubstitutedC₂-C₆₀ condensed-cyclic group; a1 through a4 are each independently aninteger of 0 to 3; b1 through b4 are each independently an integer of 1to 5; c and d are each independently an integer of 0 to 3; X₁ throughX₁₀ are each independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, hydrazine, hydrazone, a carboxyl group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, —Si(R₂₁)(R₂₂)(R₂₃), or —N(R₂₄)(R₂₅); R₂₁ through R₂₅ are eachindependently hydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted orunsubstituted C₆-C₆₀ arylthio group, or a substituted or unsubstitutedC₂-C₆₀ heteroaryl group; Z₂₁ and Z₂₂ are each independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, hydrazine, hydrazone, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, or asubstituted or unsubstituted C₁-C₆₀ alkoxy group; u is an integer of 1to 4; and v is an integer of 1 to
 6. 2. The condensed-cyclic compound ofclaim 1, wherein R₁₁ through R₁₄ are each independently hydrogen,deuterium, a substituted or unsubstituted C₁-C₁₀ alkyl group, asubstituted or unsubstituted phenyl group, a substituted orunsubstituted pentalenyl group, a substituted or unsubstituted indenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted azulenyl group, a substituted or unsubstituted heptalenylgroup, a substituted or unsubstituted indacenyl group, a substituted orunsubstituted acenaphthyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted phenalenyl group, asubstituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthryl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenylenyl group,a substituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstitutednaphthacenyl group, a substituted or unsubstituted picenyl group, asubstituted or unsubstituted perylenyl group, a substituted orunsubstituted pentaphenyl group, a substituted or unsubstitutedhexacenyl group, a substituted or unsubstituted cyclopentyl group, asubstituted or unsubstituted cyclohexyl group, a substituted orunsubstituted cycloheptyl group, a substituted or unsubstituteddihydronaphthyl group, a substituted or unsubstituted tetrahydronaphthylgroup, or a substituted or unsubstituted dihydro-indenyl group.
 3. Thecondensed-cyclic compound of claim 1, wherein Ar₁ through Ar₄ are eachindependently a substituted or unsubstituted benzene linking group, asubstituted or unsubstituted pentalene linking group, a substituted orunsubstituted indene linking group, a substituted or unsubstitutednaphthalene linking group, a substituted or unsubstituted azulenelinking group, a substituted or unsubstituted heptalene linking group, asubstituted or unsubstituted indacene linking group, a substituted orunsubstituted acenaphthylene linking group, a substituted orunsubstituted fluorene linking group, a substituted or unsubstitutedphenalene linking group, a substituted or unsubstituted phenanthrenelinking group, a substituted or unsubstituted anthracene linking group,a substituted or unsubstituted fluoranthene linking group, a substitutedor unsubstituted triphenylene linking group, a substituted orunsubstituted pyrene linking group, a substituted or unsubstitutedcrycene linking group, a substituted or unsubstituted naphthacenelinking group, a substituted or unsubstituted pycene linking group, asubstituted or unsubstituted perylene linking group, a substituted orunsubstituted pentacene linking group, or a substituted or unsubstitutedhexacene linking group.
 4. The condensed-cyclic compound of claim 1,wherein a₁ through a₄ are each independently 0, 1, or 2, and b₁ throughb₄ are each independently 1 or
 2. 5. The condensed-cyclic compound ofclaim 1, wherein R₁₁ through R₁₄ are each independently one of hydrogen;deuterium; a C₁-C₁₀ alkyl group; a phenyl group; a naphthyl group; aphenanthrenyl group; a fluorenyl group; a pyrenyl group; a cyclopentylgroup; a cyclohexyl group; a tetrahydronaphthyl group; a dihydro-indenylgroup; and a phenyl group, a naphthyl group, a phenanthrenyl group, afluorenyl group, a pyrenyl group, a cyclopentyl group, a cyclohexylgroup, a tetrahydronaphthyl group, and a dihydro-indenyl group that aresubstituted with at least one of deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group,hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, and —Si(Q₁)(Q₂)(Q₃); Q₁ through Q₃ are eachindependently a C₁-C₁₀ alkyl group or a C₆-C₁₄ aryl group; Ar₁ throughAr₄ are each independently represented by one of Formulae 3A through 3Gbelow:

wherein Z₁₁ through Z₁₄ are each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group; s is an integer of 1 to6; and t is an integer of 1 to
 3. 6. The condensed-cyclic compound ofclaim 1, wherein at least one of a combination of R₁ and R₂ and acombination of R₃ and R₄ in Formula 1 is linked to each other.
 7. Thecondensed-cyclic compound of claim 1, wherein at least one of —N(R₁)(R₂)and —N(R₃)(R₄) in Formula 1 is represented by one of Formulae 5A through5F:

wherein Z₃₁ through Z₄₂ are each independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, hydrazine, hydrazone, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, a phosphoric acidor a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, or a substituted or unsubstitutedC₁-C₆₀ alkoxy group, or a substituted or_unsubstituted C₆-C₆₀ arylgroup; and w and x are each independently an integer of 1 to
 8. 8. Thecondensed-cyclic compound of claim 1, wherein the condensed-cycliccompound is one of Compounds 1A to 3A, 74 and 5A to 30A:


9. An organic light-emitting diode comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerinterposed between the first electrode and the second electrode; whereinthe organic layer comprises at least one of the condensed-cycliccompound according to claim
 1. 10. The organic light-emitting diode ofclaim 9, wherein the organic layer comprises a hole injection layer, ahole transport layer, a functional layer having hole injection and holetransport abilities, an emission layer, an electron transport layer, anelectron injection layer, or any combination thereof.
 11. The organiclight-emitting diode of claim 10, wherein the emission layer comprisesthe condensed-cyclic compound.
 12. The organic light-emitting diode ofclaim 11, wherein the emission layer further comprises a host and thecondensed-cyclic compound in the emission layer acts as a dopant. 13.The organic light-emitting diode of claim 12, wherein the host comprisesan anthracene-based compound represented by Formula 60 below:

wherein Ar₁₁ and Ar₁₂ are each independently a substituted orunsubstituted C₆-C₆₀ arylene group; Ar₁₃ and Ar₁₄ are each independentlya substituted or unsubstituted C₁-C₁₀ alkyl group or a substituted orunsubstituted C₆-C₆₀ aryl group; and e and f are each independently aninteger of 0 to
 5. 14. The organic light-emitting diode of claim 10,wherein the electron transport layer comprises an electron transportorganic compound and a metal-containing material.
 15. The organiclight-emitting diode of claim 14, wherein the metal-containing materialis a lithium complex.
 16. The organic light-emitting diode of claim 10,wherein the organic layer comprises a hole injection layer, a holetransport layer, a functional layer having hole injection and holetransport abilities, or any combination thereof, and at least one of thehole injection layer, the hole transport layer, and the functional layerhaving hole injection and hole transport abilities comprises acharge-generating material.